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Synthesis of 1-Aza-cryptophycin 1, an Unstable Cryptophycin. An Unusual Skeletal Rearrangement
✍ Scribed by Russell A Barrow; Richard E Moore; Lian-Hai Li; Marcus A Tius
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 228 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
AbstractÐA total synthesis of cryptophycin 337 (1-aza-cryptophycin 1, 2), an analogue of the potent antitumor antibiotic cryptophycin 1 (1), is described. Cryptophycin 337 was unstable and underwent an unexpected skeletal rearrangement. (R)-Mandelic acid was used as the sole source of asymmetry for the synthesis of unit A.
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## Abstract Tunichrome __Sp‐1__ is a modified pentapeptide from the ascidian __Styela plicata__, having the structure H‐DOPA‐DOPA‐Gly‐Pro‐dcΔDOPA (where DOPA = 3,4‐dihydroxyphenylalanine and dcΔDOPA = decarboxy‐(__E__)‐α,β‐dehydro‐DOPA). The tandem mass spectrum of the peptide is dominated by a num